The Garage

My little session with Mikey meant I was a little behind on my paperwork, so I went early to work and headed straight up to the office to get started.  I grabbed myself a coffee and tidied up the papers, which got rearranged by Mikey when I fucked him over my desk. I sat down and got to business as I watched the men arrive through the office's two-way mirror window. Mikey arrived a little late and was walking a little less tall. He looked up at the office as he arrived. As he did, a large smile appeared, but I was not sure if he was for me or because he was thinking about what went down last night, he continued and went straight to his station. 

I was surprised by a knock. Part of me hoped it was Mikey, but it was my second in charge, Jimmy.  His hulking form was taking up the doorway. Jimmy was one of the hottest guys at the shop.  With oversized muscles,  everything he wore stretched and emphasized his form. This, along with his deep blue eyes and pornstar ‘stache, made it hard not to look at him and think about sex. Unsurprisingly, he needed to use our office “overtime” the most. Customers would hit on him constantly, so he always encouraged them to come back after the shop closed to pick up their vehicles. He would call out overtime at least once a week. I swear some customers broke their cars on purpose. 

As I was always working late, I occasionally saw some of the action he got up to through the two-way mirror. Jimmy was one who particularly liked to fuck where I could see it all, especially when the customer was a man. I think he thought that since I was gay I'd enjoy those most,  although honestly, I loved just watching him fuck, period. It didn't matter if they were a man or a woman. What most of the guys in the shop didn't know was that although he got many customers to come back late, not all could go through with it.  You see Jimmy's cock was big, a decent 9 inches long but super thick. Inevitably, the first time people saw his dick their eyes would widen and they would gasp in horror at the thought of that thing trying to fuck them.  

Once the shock subsided, many would try but only a subset would succeed. When people gave up, Jimmy had to settle for a blow job, although even there many struggled.  For those that could take him,  they were rewarded with a solid fucking. He'd always start slow, but once they were used to his size, Jimmy took off, using the full force of his muscle.  He pounded their pussy or arse like a beast. Screams of ecstasy were a certainty when Jimmy was fucking someone. All his customers left sore but happy, and many returned asking for him specifically to fix their car.  

When I saw Jimmy at my office door, I thought Mikey had told him what happened and he was here to get the dirt, but actually, it was the reverse. The boys were all eager to know what went down on Mikey's first overtime but he was being tight-lipped. I respected Mikey’s decision and told Jimmy that Mikey did it out of sight of the two-way mirror. Jimmy gave me a long hard stare.  I've known Jimmy for a long time and so I knew that he knew I was lying. But he respected that, smiled, said okay, and went back to work.

I did my rounds a little later than usual. I always chatted with everyone, so no one thought much of it when I checked in with Mikey. I made sure when I reached him that he was out of earshot of the other boys. I asked him how he was doing. He just smiled and said still feeling the residuals of last night's punishment.  I told him good, and followed up with, you need to work through it like a man. I smiled and winked at him to let him know I was somewhat kidding, but he got it.  

As I was about to walk away he asked,  when was he to expect the rest of his punishment? I looked at him and smiled. I remembered last night I jokingly told him that since he had cum during his punishment, it was null and void. Clearly, he was hoping that was not a joke. I told him that maybe we can wait til tomorrow since his arse was still raw.  He smiled but then said, fine, although he preferred  it more raw. This time it was his turn to smile and wink as I walked away.

As I completed my rounds, I ended with Jimmy. The first words out of his mouth were, you really are not going to tell me what happened. I just smiled and said No!, I respect the boy's discretion. He looked at me with one of his sexy side looks which I interpreted as how can you be doing this to me bruh. I was dying to tell him, but want to be discrete. So I said, okay, why don't you stop by after work tomorrow and I can tell all. I told him that Mikey's customer is coming back, so maybe once Mikey's done with them, he can join me in the office to share a cigar and whiskey and I'll dish. He smiled and said deal.

 The rest of the day was uneventful and everyone went home early.  I stayed a little later to try and get ahead of my paperwork ready for tomorrow but left early too. 

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The next day, the anticipation was palatable. Although neither knew what I had planned for them, Jimmy and Mikey kept catching my eye and smiling my way whenever I walked through.  When  I stopped at Mikey's station, I reminded him to call overtime so the boys knew to leave early.  Later that day he did it,  and Jimmy looked at me and smiled. Mikey caught the stare but I assumed he expected this from the guys in the shop, as they all would ultimately be imagining the action that might be going down tonight. 

Jimmy’s motorcycle was the first to leave, and most other guys were quick to follow.  Mikey was cleaning up, but trying a little too hard to be casual.  I barely lit my cigar before I heard him run up the stairs and knock on my door.  He didn't wait for a response and he walked in all eager and excited. I looked at him and said, come over here, tapped my knees, and encouraged him to take a seat. I took this opportunity to enjoy my cigar and stare at him.  I could see the pause made him unsettled as he could not tell what was going to happen next. I puffed on my cigar and enjoyed having him near me.

I told him that I was going to help him show more control.  With that, I moved my hand over to his groin. I could feel his semi-hard cock through his jeans.  I slowly undid his button and zipper. I noticed today he was wearing a sexy jockstrap.  I looked up at him and smiled.  He said he was ready for me.  He stood up as I pulled down his jeans. In my seated position, his groin was just at eye level. With a cigar between my lips, I continued to caress his cock, feeling it expand in the fabric of his jockstrap. The whole time I maintained eye contact with him, building the intensity of the moment. 

I could see the anticipation on his face. I took the cigar from my mouth and said I was going to help him so he did not lose his load when he was being punished this time.  With that, I released his cock from the confines of his jockstrap.  I had wanted a closer look at the boy's cock for two days now. The last time I pulled off his jeans I could tell that this boy had some impressive meat on him but was in too much of a rush to give it the attention I wanted. Seeing it in front of me, it was as beautiful as I remembered. It was so long and thin you could grasp it fully with your hand and still his thick bulbous head would sit comfortably inches above your fist.

With it firmly in my grasp,  I brought his sweaty dick up to my face, precum glistening on the tip. I took in the aroma, I then took the tip of my cigar and rolled it on the head of his cock, covering it with his precum until it was dribbling off the end. I brought it back to my mouth, and inhaled, savoring the flavor of the boy as I took in the smoke of my cigar. I was in fucking heaven. I momentarily released the boy's cock, took another inhale and held in the smoke. I took the cigar from my lips, grabbed the boy's hips with both hands and pulled him forward so his cock was close to my lips. As I exhaled my smoke, I slowly went down on him. The smoke enveloped his cock as my lips did the same.

I used my hands to bring the boy forward, forcing his cock down my throat. Although he was a big boy, my years of experience allowed me to take him down in one smooth action. I buried my nose into his groin and inhaled him. I could hear the boy moan, as I slowly released his cock. Once back at his bulbous head, I stopped, slowly working it with my tongue encouraging him to release more precum. Although I could have happily worked his dick for hours, I knew I did not have much time, so started to work his shaft with my hand keeping my lips on the tip of his cock. I aggressively masturbated the boy, playing with him til I found the rhythm and strength that seemed to work the best. As his moans became more intense and faster, I worked harder.

I knew it would not take long to get this young stud to cum. Within minutes he was gushing in my mouth, his hot creamy jizz hit the back of my throat as he filled my gullet with his seed. Once he came to a stop I looked up at him, gave him one good look at my mouth filled with his cum, and swallowed. I then took my cigar, put it back to my lips, and inhaled. I stood up and stared at him. He was spent. I then told him, now we can get ready for your punishment to begin. With that, I spun him around with one hand and pushed his head down onto the table exposing his arse once again over the end of my desk. With Cigar in my mouth, I slowly ran my fingers over his sphincter, allowing my fingers to probe his arse. One, then two, and finally three fingers stretching his hole.

Mikey started to moan in excitement and anticipation of what was to come. He knew that I was about to give him the hard raw fucking he was wanting. My cock was rock hard from our pregaming, so I whipped it out with one quick motion and rammed it up the boy's arse. Not giving the boy time to prepare. I then pulled it out slowly, only to quickly ram it back it in fast, making sure the boy felt my cock go deep. It was then that I heard a motorcycle pull up. Mikey squirmed as he realized that soon we would no longer be alone. I told him to calm down, it was all good. I have found the tool that would give him the punishment he needed. He looked at me concerned, but I smiled at him reassuringly and he relaxed. 

I heard the heavy footsteps of Jimmy’s boots approaching the office. He did not even knock as he walked in. He stood there in a leather jacket and tight jeans looking like a beast of a man. The shocked look on Jimmy’s face seeing me balls deep in Mikey made me smile. He looked down and saw Mikey had a nervous look on his face. I did not miss a beat, as I continued to pound Mikey, and told Jimmy that Mikey here, needed to be punished and I knew he was the guy to give it to him. He then looked up at me and smiled and said, is that so? As he said this, he looked down at Mikey to see if he agreed. Mikey just smiled and said, I was such a bad boy after all. Jimmy returned the smile.

With that, I told him to pull out his cock so Mikey could see what we had in store for him.  Even semi-hard, Jimmy’s cock was impressive. As he took it out from his jeans, I could hear Mikey inhale at the sight. I told Jimmy to come around so that Mikey could get that beast ready. Jimmy came around the desk so his cock was up in Mikey’s face. Without missing a beat, Mikey took that semi-hard cock into his mouth, sucking on it like a beast. As it grew, Mikey took the expanding girth like a pro. It was clear that this boy knew how to work a dick, no matter how big. With his mouth full of cock, I continued to pound his arse, Jimmy and I smiled across at each other as we spit-roasted the boy. 

I wanted to kiss Jimmy so bad at this time but knew this was not appropriate, so I took my cigar from my lips and handed it to him. He took a long inhale and stared down at the boy on his cock as he exhaled.  As I pulled my cock from the boy's hole, I told Jimmy,  now was a good time to punish the boy for breaking the laptop. Jimmy made his way around the desk.

Mikey's face changed as he knew what was about to happen and knew too well that this was going to hurt. Jimmy started to play with the boy’s hole, fingering it. I then reminded Jimmy this was meant to be a punishment not sex, and besides I had already stretched it too much for him. He smiled at me, and said okay let’s do this. He did not waste a moment and lined up his cock with Mikey’s red and throbbing hole. Without warning he rammed his cock straight into the boy with one large motion

Mikey let out a scream of pain. Jimmy stopped. I asked Mikey if he was man enough to take his punishment. Sweaty and exhausted, he replied, yes sir. With that, I told Jimmy to continue. As I have seen him do many times before, Jimmy then went to town on the boy’s arse, pounding it like an animal. The rhythm of Jimmy’s fucking was intense. It is clear that Jimmy likes to give it rough and hard, but does not get to very often. Mikey’s groans of pleasure were mixed with intense pain, but he kept encouraging Jimmy to fuck him harder. Jimmy did not disappoint and kept going, harder and harder. The atmosphere in the office was electric. I sat back in my chair, watching these two men fucking and smoking a fresh gar. It was one of the most intense experiences I have ever had.

I could see that Jimmy was getting close. He started to slow down. I asked him what he was doing. He said that he was about to cum, and wasn’t sure if he should come up the boy’s arse. Before I could say anything, Mikey said, please do Sir. With that Jimmy resumed his pace and then within minutes was cumming inside the boy. With each shot, his body convulsed and he leaned more forward until he collapsed on Mikey, his full weight pushing the boy down. Once done, he stood up and pulled his now semi-erect cock out of the boy’s hole. The boy remained prostrate on the table exhausted, as I knelt behind the boy. As Jimmy watched, I told the boy he could release Jimmy’s seed, which I caught with my tongue. I lapped up all that the boy could release, using my tongue to soothe the boy’s red, and sore the hole,  as he caught his breath. 

When I was done, we all stood up and stared at each other and smiled.  It was then that I noticed that again, there was cum on Mikey’s chest and the table. I looked up at Mikey. He just smiled as he realized he was caught. He said, sorry Sir, I guess i like being punished too much. I smiled back, well Jimmy and I will have to think about how we can fix that problem. For the time being, Jimmy and I will just have to sit here and finish our cigar and whiskey, while you clean up. Sweaty and half naked, Mikey just smiled and went to work, while his bosses watched.